Like many of Tuscany and Umbria’s historic hilltop towns, Cortona is a very difficult place to build, or alter buildings, so many of the best places to stay in Cortona are elegantly converted palazzo, or simple townhouses. Around the vineyard-laden hills are a further range of accommodation options in converted villas, hunting lodges and farmhouses, which are perfect if you’re looking for more of a rural retreat, or a base for exploring the whole region, or you plan to do some driving.
Cortona is still probably best known for being the setting of the book, and subsequent film adaptation, ‘Under the Tuscan Sun’, but before that it was still one of Tuscany’s most beautiful Medieval walled towns, with stunning views of the Val di Chiana, and much more besides. Culture vultures will love its museums and beautiful architecture, whilst everyone will enjoy wandering its pretty streets and stopping off at the many shops, bars and restaurants along the way.
Just be warned that in peak season this town is extremely busy. So if you want to guarantee a room in one of the best places to stay in Cortona you'll need to book well ahead.